Thiophenol → HCID 53778325, compound

Participants

Reaction Conditions

Reaction Steps

N-(tert-butoxycarbonyl)-4-(3-azidopropyl)-L-proline ethyl ester (1.17 g, 3.58 mmol) was dissolved in anhydrous tetrahydrofuran (40 mL) and dry tin chloride (1.01 g, 1.5 eq.), thiophenol (2.21 mL, 6 eq.) and triethylamine (2.24 mL, 4.5 eq.) were added. The reaction mixture was stirred at 25° C. for Ihour, poured into ethyl acetate, washed with 1 N HCl, 1 N NaOH, brine, dried (Na2SO4) and concentrated. The residue (0.96 g, 90%) was used crude in the next step: 1H NMR (400 MHz, CDCl3, 7:3 mixture of diastereomers) δ 1.29 (m, 3H), 1.40-1.56 (m, 9H), 1.84 (m, 1H), 2.10 (m, 1H), 2.39 (m, 1H), 2.42 (m, 1H), 2.72 (m, 2H), 2.99 (m, 2H), 3.76 (m, 2H) 4.18-4.38 (m, 4H).

Provenance & Evidence